03E17 - Catch-22

Desmond's latest fragmented vision suggests that his old girlfriend, Penny, will crash-land onto the island. Desmond organizes a posse of himself, Hurley, Jin, and Charlie to come along with him into the jungle expecting Penny to parachute onto the island. But the vision also suggests that Charlie will die by stumbling upon a trip-wire if he comes along with them. But Desmond insists that Charlie must come along to make the vision come true. Meanwhile, Desmond recalls his days in a monastery in Scotland over 10 years earlier after leaving his old fiancée, Ruth, a few days before their wedding where he later met Penny. In the present, Kate attempts to flirt with Jack, but he instead has eyes for Juliet, and Kate has another one-night stand with Sawyer.